title: Stereostructure reassignment and determination of the absolute configuration of pericosine D(o) by a synthetic approach.
abstract: A combination of chemical synthesis and NMR methods was used to reassign the structure of pericosine D(o) (8), a cytotoxic marine natural product produced by the fungus Periconia byssoides OUPS-N133 that was originally derived from the sea hare Aplysia kurodai. Chemical synthesis was used to prepare pericoisne D(o) (8) from a known chlorohydrin that was in turn derived from (-)-quinic acid. The absolute configuration of natural pericosine D(o) (8) was determined to be methyl (3R,4S,5S,6S)-6-chloro-3,4,5-trihydroxy-1-cyclohexene-1-carboxylate. HPLC analyses using a chiral-phase column indicated that pericosine D(o) (8) exists in an enantiomerically pure form in nature.
authors.affiliation: Laboratory of Pharmaceutical Organic Chemistry, Osaka University of Pharmaceutical Sciences, 4-20-1 Nasahara, Takatsuki, Osaka 569-1094, Japan. usami@gly.oups.ac.jp
authors.forename: Yoshihide
authors.initials: Y
authors.lastname: Usami
authors.forename: Koji
authors.initials: K
authors.lastname: Mizuki
mesh_terms: D000818:Animals; D001048:Aplysia / Q000382:microbiology; D001203:Ascomycota / Q000737:chemistry*; D006801:Humans; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D011801:Quinic Acid / Q000737:chemistry; D012765:Shikimic Acid / Q000031:analogs & derivatives / Q000138:chemical synthesis / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: C559021:pericosine D(o); D011801:Quinic Acid; D012765:Shikimic Acid